2',7'-Dichlorofluorescein

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2',7'-Dichlorofluorescein

2',7'-Dichlorofluorescein | 76-54-0

Catalog Number A17-0109
Category Fluorescein FAM
Molecular Formula C20H10Cl2O5
Molecular Weight 401.20
Catalog Number Size Price Quantity

Product Introduction

2',7'-Dichlorofluorescein can be used in the synthesis of 2',7'-Dichlorodihydrofluorescein, which is a cell-permeable non-fluorescent probe.

Chemical Information

Synonyms 2',7'-dichloro-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; 2',7'-Dichlorofluorescein; Fluorescein 27; Fluorescein 548
IUPAC Name 2',7'-dichloro-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
Canonical SMILES C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C=C4OC5=CC(=C(C=C35)Cl)O)O)Cl
InChI InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H
InChI Key VFNKZQNIXUFLBC-UHFFFAOYSA-N
  • Product Specification
  • Application
Signal Warning
GHS Hazard Statements H315 (90.91%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement Codes P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.)

2’,7’-Dichlorofluorescein (DCF) is a chlorinated derivative of fluorescein, a compound that is widely used as a fluorescent tracer and dye due to its bright green fluorescence and high quantum yield. Structurally, DCF contains two chlorine atoms attached to the fluorescein backbone at the 2’ and 7’ positions, which influence its optical and chemical properties. DCF itself is generally non-fluorescent until it undergoes cellular processes or chemical reactions that enable its conversion to a fluorescent form. This characteristic makes it useful in various biochemical and analytical applications.

One of the primary applications of 2’,7’-Dichlorofluorescein is in the detection and measurement of reactive oxygen species (ROS) within biological systems. When DCF is oxidized by ROS, it transforms into the highly fluorescent 2’,7’-dichlorofluorescein diacetate (DCFH-DA), making it a valuable tool for monitoring oxidative stress in cells and tissues. This process is crucial for studying the effects of oxidative stress-related diseases and assessing the efficacy of antioxidant therapies.

Additionally, 2’,7’-Dichlorofluorescein is utilized in cellular imaging techniques due to its ability to penetrate cell membranes. Once inside the cells, it can react with intracellular ROS to emit fluorescence, thereby serving as a vital tool for visualizing cellular events and mechanisms in real-time. This application is especially pertinent in research involving cancer, neurodegenerative diseases, and aging, where oxidative stress plays a significant role.

In environmental science, DCF finds application as a marker to assess the oxidative potential of various environmental samples. It helps in evaluating the presence of pollutants and their impact on oxidative stress in aquatic ecosystems. This is achieved by measuring the fluorescence signal resulting from the interaction between DCF and ROS in the sample, which provides insights into the sample’s oxidative properties.

Lastly, DCF is instrumental in the pharmaceutical industry, particularly in drug development and screening. By using DCF-based assays, researchers can rapidly assess the oxidative properties of new drug compounds and their potential cytotoxic effects. This accelerates the identification of promising therapeutic agents and helps in optimizing their safety and efficacy profiles before clinical trials.

Computed Properties

XLogP3 4.7
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 0
Exact Mass 399.9905288 g/mol
Monoisotopic Mass 399.9905288 g/mol
Topological Polar Surface Area 76Ų
Heavy Atom Count 27
Formal Charge 0
Complexity 585
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
34958783 2022-01-15 Effect of major components of Tripterygium wilfordii Hook. f on the uptake function of organic anion transporting polypeptide 1B1 Toxicology and applied pharmacology
22910297 2012-11-01 Oxidative effects of nanosecond pulsed electric field exposure in cells and cell-free media Archives of biochemistry and biophysics
22939937 2012-11-01 Proinflammatory activation of macrophages by bisphenol A-glycidyl-methacrylate involved NFκB activation via PI3K/Akt pathway Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
22940460 2012-11-01 Assessment of the role of in situ generated (E)-2,4-diene-valproic acid in the toxicity of valproic acid and (E)-2-ene-valproic acid in sandwich-cultured rat hepatocytes Toxicology and applied pharmacology
23022691 2012-11-01 Nuclear targeting terpyridine iron(II) complexes for cellular imaging and remarkable photocytotoxicity Journal of inorganic biochemistry

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